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Moshe discusses in Devarim how the people were supposed to approach the Mountain of the Amorite and conquer the land. Then, after

Where is this mountain geographically? Does it have any special significance halachically or in aggada?

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Perhaps by way of introduction one should first refer to Bamidbar 13:29 where it writes:

עֲמָלֵ֥ק יוֹשֵׁ֖ב בְּאֶ֣רֶץ הַנֶּ֑גֶב וְ֠הַֽחִתִּי וְהַיְבוּסִ֤י וְהָֽאֱמֹרִי֙ יוֹשֵׁ֣ב בָּהָ֔ר וְהַֽכְּנַעֲנִי֙ יֹשֵׁ֣ב עַל־הַיָּ֔ם וְעַ֖ל יַ֥ד הַיַּרְדֵּֽן׃

"Amalekites dwell in the Negeb region; Hittites, Jebusites, and Amorites inhabit the hill country; and Canaanites dwell by the Sea and along the Jordan.” (Sefaria Translation)

So it is clear that Emorim dwelt specifically in a mountainous region.

The Netziv in his Ha'amek Davar on the possuk in Devarim 1:7 that you bring alludes to the strategic geographical point that the Emorim held by being in the mountains. In this analysis he notes how the Mountain of the Emorite was: דרך הר האמורי שהוא הר יהודה בדרום ארץ ישראל... - i.e. it was in the southern part of the land of Israel.

When further researching this - I came across a pasuk in Amos 2:9 where it writes:

וְאָ֨נֹכִ֜י הִשְׁמַ֤דְתִּי אֶת־הָֽאֱמֹרִי֙ מִפְּנֵיהֶ֔ם אֲשֶׁ֨ר כְּגֹ֤בַהּ אֲרָזִים֙ גָּבְה֔וֹ וְחָסֹ֥ן ה֖וּא כָּֽאַלּוֹנִ֑ים וָאַשְׁמִ֤יד פִּרְיוֹ֙ מִמַּ֔עַל וְשָׁרָשָׁ֖יו מִתָּֽחַת׃

"Yet I Destroyed the Amorite before them, Whose stature was like the cedar’s And who was stout as the oak, Destroying his boughs above And his trunk below!" (Sefaria translation)

The Chida in his Chomas Anach writes:

ואנכי השמדתי את האמורי וכו'. יש כמה דקדוקים בפסוקים אלו והם מורגשים. ואפשר דתחילה מדבר כנגד בני גד ובני ראובן היושבים מעבר לירדן ואליהם יאמר שלא לנכח ואנכי השמדתי את האמורי מפניהם הם סיחון ועוג אשר היו כגובה ארזים וכו' ואחר ידבר לשאר ישראל לנכח ואנכי העלתי אתכם וכו' והני בהני שייכי דהשמיד האמורי וכו' מפני כל ישראל ולכלם העלה ממצרים. רק חילוק הדברים לרמוז שמדבר לבני גד ובני ראובן ולישראל...

Yet I Destroyed the Emorite before them etc. There are many specific elements in this verse and they are noticeable. It is possible that the verse is speaking about the Bnei Gad and Bnei Reuven who dwelt in Transjordan and to them he was saying "And I destroyed the Emorite" because these were Sichon and Og who were as tall as cedars etc. and then he was addressing the rest of Bnei Yisrael "And I brought you up from the land of Egypt etc." And with each of these (i.e. Bnei Gad & Bnei Reuven as well as the rest of Bnei Yisrael) it was relevant to say that "I destroyed the Emorite" as all of Israel had been brought up from Egypt. Thus the only distinction of these words is to hint that He was talking to Bnei Gad and Bnei Reuven (on one side) and to Israel (in the next verse)..." (My translation)

So with this is mind, conceivably, this mountain range was in the South East part of the land of Israel running in line with the Transjordan region where the Bnei Reuven and Bnei Gad were situated.

This would perhaps tally with the attached map which helps illustrate the Emorite inhabited region.

enter image description here

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